What a fantastic architecture. When you do the brick, if you stain it with masonry /concrete stain you won't have the same issues of maintenance as with paint. They will spray it evenly - through you will have to select a deeper color - either taupe (brown-gray) or a straight charcoal. Love your windows and the classic angled railing. I think a dark gray on the siding will make the orange brick jump even more. What bothers me is the white (railing, fascia, eaves) juxtaposed with the earth toned stuff. So I would recommend camel tones - for the siding - something like http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6108-latte/ and the hopsack next darker tone for the garage door. Use the lighter tan for trim that is now white - http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6107-nomadic-desert/ Use the darkest tone if you are painting concrete steps. If you think you will stain your brick charcoal, then the white eaves and trim are probably right, and you may not want to paint it tan now and then go back. If your brick were charcoal, then I would block out the rest in grays and blue grays - leave the white eaves, but take the railing and posts charcoal too. A blue gray door - like sw smoky blue.

It depends on the species of wood (I.e. How hard or soft) and whether or not the ambient temperature can remain as stable as possible. What you caulk and paint in warmer weather may look great now, but when it begins to get colder, the wood begins to shrink, and the caulk will begin to pull away. This will look worse than if you didn't caulk at all. My suggestion is to use a caulk like the brand called "Big Stretch " in an attempt to avoid this.

The colour scheme and amount of paint coats you need depend on the paint brand and what you're trying to do.

Swimming pool season is upon us, rather late I might add this year, you may be considering painting your pool. There are a few things to consider is what the previous coating is and the appropriate preparation that is required. When we quote pools we generally only get to inspect them with water in them. We will always put a clause in to assess what the actual condition is like when empty, like when we found a good portion of the surface was very drummy and subsequently we had to remove a lot the surface and replanted, always be mindful of hidden costs when pool painting, they are not always straight forward.